bis[2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate, stereoisomer Chemical Properties

Melting point:

80°C

solubility 

Chloroform (Slightly), DMSO (Slightly)

form 

Solid

color 

Off-White to Pale Yellow

EPA Substance Registry System

1,3-Cyclobutanedicarboxylic acid, 2,4-diphenyl-, bis[(1R,2R,3S,5S)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] ester, (1.alpha.,2.alpha.,3.beta.,4.beta.)- (490-17-5)

bis[2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 2,4-diphenylcyclobutane-1,3-dicarboxylate, stereoisomer Usage And Synthesis

Description

From the leaves of Erythroxylon truxillense Rusby, Hesse isolated an amorphous alkaloid which he designated Cocamine. This was subsequently shown by Liebermann to be a mixture of two isomeric bases and, although the pure alkaloids have not yet been obtained from the alkaloidal mixture owing to difficulties in their separation, each has been prepared synthetically. This particular alkaloid is an amorphous white powder which is soluble in all organic solvents except light petroleum and also insoluble in H20. Solutions of the base are alllaevorotatory and have an intensely bitter taste. Acid hydrolysis with dilute HCl yields MeOH, (-)-ecgonine and Q-truxillic acid, m.p. 228°C. The alkaloid is synthesized by the action of α-truxillic anhydride on (-)-ecgonine followed by methylation of the resulting α-truxilloylecgonine.

Uses

?-Truxillin is an alkaloid found in coca leaves. It is an impurity of illicit Cocaine (C633500), which inhibits the dopamine, norepinephrine, and serotonin transporters.

References

Hesse., Pharm. Zeit., 407,668 (1887)
Liebermann., Ber., 21,2342 (1888)
Hesse., ibid, 22, 665 (1889)
Liebermann, Drory., ibid, 22,682 (1889)